# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xue038
_database_code_depnum_ccdc_archive 'CCDC 1537736'
_audit_update_record             
;
2017-03-13 deposited with the CCDC.
2017-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H9.43 Cl1.58 N O2'
_chemical_formula_sum            'C14 H9.43 Cl1.58 N O2'
_chemical_formula_weight         279.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0667(5)
_cell_length_b                   15.3771(13)
_cell_length_c                   13.1958(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.360(3)
_cell_angle_gamma                90
_cell_volume                     1228.90(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3735
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             573
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.431
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.986
##############################################################################
#                                                                            #
#  NOTE on absorbtion correction with SADABS:                                #
#                                                                            #
#  (Semi)empirical correction methods for absorption correction are more of  #
#  a problem in that they often specify only a relative correction range     #
#  [ Tmin(emp) & Tmax(emp)].                                                 #
#                                                                            #
#  Acta Cryst. procedures call in such cases for the multiplication of both  #
#  empirical values with Tmax(expected).                                     #
#                                                                            #
#  THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW!  (George                   #
#  and Ton are agruing this point!)                                          #
#                                                                            #
##############################################################################
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX 2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13634
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.068
_diffrn_reflns_theta_max         29.150
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3296
_reflns_number_gt                2307
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.3522P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3296
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9181(4) 0.40004(15) 0.28795(18) 0.0237(5) Uani 1 1 d . . . . .
O1 O 0.8712(3) 0.47593(13) 0.33942(15) 0.0266(4) Uani 1 1 d . . . . .
C1 C 0.7621(5) 0.4537(2) 0.4306(2) 0.0317(7) Uani 1 1 d . . . . .
H1A H 0.7358 0.5066 0.4693 0.048 Uiso 1 1 calc R U . . .
H1B H 0.8558 0.4139 0.4721 0.048 Uiso 1 1 calc R U . . .
H1C H 0.6207 0.4253 0.4120 0.048 Uiso 1 1 calc R U . . .
C2 C 1.1087(4) 0.35729(19) 0.3200(2) 0.0229(6) Uani 1 1 d . . . . .
O2 O 1.2288(3) 0.38485(14) 0.39158(16) 0.0292(5) Uani 1 1 d . . . . .
C3 C 1.1489(5) 0.27592(19) 0.2659(2) 0.0242(6) Uani 1 1 d . . . . .
C4 C 1.3331(5) 0.2266(2) 0.2987(2) 0.0306(7) Uani 1 1 d . . . . .
H4A H 1.4319 0.2479 0.3515 0.037 Uiso 1 1 calc R U . . .
C5 C 1.3718(5) 0.1474(2) 0.2548(3) 0.0358(7) Uani 1 1 d . . . . .
H5A H 1.4974 0.1141 0.2769 0.043 Uiso 1 1 calc R U . . .
C6 C 1.2248(6) 0.1163(2) 0.1775(3) 0.0371(8) Uani 1 1 d . . . . .
H6A H 1.2497 0.0610 0.1481 0.045 Uiso 1 1 calc R U . . .
C7 C 1.0459(5) 0.1645(2) 0.1436(2) 0.0335(7) Uani 1 1 d . . . . .
H7A H 0.9491 0.1425 0.0905 0.040 Uiso 1 1 calc R U . . .
C8 C 1.0030(5) 0.24607(19) 0.1861(2) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.8124(5) 0.2998(2) 0.1541(2) 0.0249(6) Uani 1 1 d . . . . .
C10 C 0.6647(5) 0.2782(2) 0.0718(2) 0.0331(7) Uani 1 1 d . . . . .
H10A H 0.6891 0.2271 0.0337 0.040 Uiso 1 1 calc R U . A 2
Cl11 Cl 0.3094(2) 0.30733(11) -0.05574(11) 0.0404(5) Uani 0.575(4) 1 d . . P B
1
C11 C 0.4853(5) 0.3301(2) 0.0456(2) 0.0365(8) Uani 1 1 d . . . C 2
H11A H 0.3866 0.3145 -0.0100 0.044 Uiso 0.425(4) 1 calc R U P B 2
C12 C 0.4489(5) 0.4049(2) 0.1006(2) 0.0329(7) Uani 1 1 d . . . . .
Cl12 Cl 0.22204(14) 0.47048(7) 0.06929(7) 0.0467(3) Uani 1 1 d . . . . .
C13 C 0.5897(5) 0.4295(2) 0.1811(2) 0.0271(6) Uani 1 1 d . . . . .
H13A H 0.5637 0.4811 0.2181 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7721(4) 0.37664(19) 0.2069(2) 0.0235(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.375(3) . ?
N1 O1 1.388(3) . ?
N1 C14 1.395(3) . ?
O1 C1 1.448(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.234(3) . ?
C2 C3 1.468(4) . ?
C3 C4 1.398(4) . ?
C3 C8 1.412(4) . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.368(5) . ?
C6 H6A 0.9500 . ?
C7 C8 1.404(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.463(4) . ?
C9 C14 1.400(4) . ?
C9 C10 1.406(4) . ?
C10 C11 1.377(5) . ?
C10 H10A 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.377(4) . ?
C12 Cl12 1.736(3) . ?
C13 C14 1.400(4) . ?
C13 H13A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 O1 116.4(2) . . ?
C2 N1 C14 126.7(2) . . ?
O1 N1 C14 116.9(2) . . ?
N1 O1 C1 108.9(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 121.3(3) . . ?
O2 C2 C3 123.9(3) . . ?
N1 C2 C3 114.7(2) . . ?
C4 C3 C8 120.6(3) . . ?
C4 C3 C2 117.6(3) . . ?
C8 C3 C2 121.7(3) . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5A 120.2 . . ?
C6 C5 H5A 120.2 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C8 121.1(3) . . ?
C6 C7 H7A 119.5 . . ?
C8 C7 H7A 119.5 . . ?
C7 C8 C3 117.7(3) . . ?
C7 C8 C9 123.4(3) . . ?
C3 C8 C9 118.8(3) . . ?
C14 C9 C10 117.5(3) . . ?
C14 C9 C8 119.4(2) . . ?
C10 C9 C8 123.1(3) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10A 119.5 . . ?
C9 C10 H10A 119.5 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C13 C12 C11 121.4(3) . . ?
C13 C12 Cl12 118.1(3) . . ?
C11 C12 Cl12 120.4(2) . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13A 120.8 . . ?
C14 C13 H13A 120.8 . . ?
N1 C14 C13 119.6(3) . . ?
N1 C14 C9 118.5(2) . . ?
C13 C14 C9 121.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 O1 C1 -83.5(3) . . . . ?
C14 N1 O1 C1 98.8(3) . . . . ?
O1 N1 C2 O2 0.9(4) . . . . ?
C14 N1 C2 O2 178.4(3) . . . . ?
O1 N1 C2 C3 178.2(2) . . . . ?
C14 N1 C2 C3 -4.4(4) . . . . ?
O2 C2 C3 C4 0.8(4) . . . . ?
N1 C2 C3 C4 -176.3(3) . . . . ?
O2 C2 C3 C8 178.3(3) . . . . ?
N1 C2 C3 C8 1.1(4) . . . . ?
C8 C3 C4 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 176.2(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 1.4(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C3 -0.9(5) . . . . ?
C6 C7 C8 C9 -179.0(3) . . . . ?
C4 C3 C8 C7 1.9(4) . . . . ?
C2 C3 C8 C7 -175.5(3) . . . . ?
C4 C3 C8 C9 -179.9(3) . . . . ?
C2 C3 C8 C9 2.7(4) . . . . ?
C7 C8 C9 C14 174.4(3) . . . . ?
C3 C8 C9 C14 -3.7(4) . . . . ?
C7 C8 C9 C10 -5.7(5) . . . . ?
C3 C8 C9 C10 176.3(3) . . . . ?
C14 C9 C10 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 178.8(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 0.5(5) . . . . ?
C10 C11 C12 Cl12 -179.4(2) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
Cl12 C12 C13 C14 179.7(2) . . . . ?
C2 N1 C14 C13 -177.1(3) . . . . ?
O1 N1 C14 C13 0.3(4) . . . . ?
C2 N1 C14 C9 3.5(4) . . . . ?
O1 N1 C14 C9 -179.1(2) . . . . ?
C12 C13 C14 N1 179.8(3) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C10 C9 C14 N1 -179.1(3) . . . . ?
C8 C9 C14 N1 0.9(4) . . . . ?
C10 C9 C14 C13 1.4(4) . . . . ?
C8 C9 C14 C13 -178.6(3) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.068

